Gamblers is a podcast about men and women who live by their wits and wagers. People who bet big on themselves, and won. From a road-hustling pool shark to a punk-rock horse handicapper to a sports bettor who could move lines, the six-part anthology series focuses on the fascinating lives of professional underground gamblers and how they make their money.
Maybe your only experience with the racetrack is at your local hardscrabble race course, where a weekday card might draw 4,000 or 5,000 fans, mostly from the retiree set, chomping cigars and riding around on rascal scooters. That’s not where my producers and I are. We’re at the Santa Anita Racetrack in Arcadia, California, one of the most storied racetracks in America. And we’re here on the holiest of Saturdays, the Breeders’ Cup, which is essentially horse racing’s world championship. The crowd is large, jubilant, and for the most part well dressed and mannered.
The grandstands look out onto the San Gabriel Mountains, about as beautiful a view as there is in all of sports. There are over 67,000 people here, and they are betting with both hands. But whether the crowd are cigar chompers or seersuckers, Emily Gullikson still stands out. There just aren’t very many people like her in this world, a world that has long been dominated by men that are buttoned up and straightlaced, men that are conservative in appearance and outlook, and men that are … well … men.
You might see a lot of horses with “Renegade” in their names, but you don’t see too many Emilys with “Renegade” tattooed across their knuckles at the racetrack. There is only one. And she is more than just a racetrack gambler. She does roller derby. She’s into CrossFit. She’s got a lot more piercings than most folks at the track. She’s into punk and hardcore, a straight-edger who refuses to drink alcohol or touch drugs. She’s someone who looks like she’d be more at home in the pit than in the paddock.
Be that as it may, when it comes to picking winners, Emily is undeniably one of the best. She’s a regular competitor in the top horse-race-betting tournaments across the country, but there’s nothing regular about her talent. Emily is so good that some of the best gamblers in the country have sought her advice and counsel.
“We were a team, then we had a fight at the NHC and we were no longer a team,” says Alan Denkenson, or “Dink.”
Among sports gamblers, Dink is a legend. Bruce Willis played him in the 2012 movie Lay the Favorite. Though he’s one of the most successful gamblers in America, when he competed in one of the biggest horse-race-betting tournaments ever, the National Handicapping Championship, he asked Emily to be on his team.
“We got in,” Denkenson says. “I did as much work as I could thinking I could do it all in one night and it took me like 40 minutes a race so I’m like, ‘Oh my God.’ So I did like eight races and I showed them my work, and [Emily] was mad at me, and I go, ‘Well, you’re better than me. You just do the whole thing.’”
Dink wasn’t the only gambler seeking Emily’s advice on betting horses. She sells her insights on horse racing to some of the other top gamblers in the world through her company Optix-EQ. And she’s paid by a number of racetracks in the U.S. and Canada to handicap races and share her selections with their guests. These are the top horseplayers in the country, many of whom consider themselves geniuses, yet they’re willing to pay Emily for her information, and that says a lot about how good she is at this game.
“I think she’s quite the handicapper and quite the gambler,” says Garett Skiba, a top handicapper who has racked up more six-figure tournament cashes in the last couple of years than any other player. He and Emily met after sitting next to each other during a tournament where they were competitors. Now they’re friends, and he pays big money for Emily’s trip notes to help him with his plays.
“She does a lot more race watching, trip handicapping,” says Skiba. “The benefit is that she works for Optix and I’m able to use some of that to my advantage. And so it probably handicaps her to some degree to kind of put all her best thoughts on paper.”
What Garett is saying is that he utilizes her handicapping data because he buys it from her. The work that she’s doing to handicap the races he already has the benefit of.
“I like to put as much information as I can together to formulate opinion,” Skiba says. “And so, obviously her information—as she watches so many races—is important to the overall plays that I’m going to make on that given day.”
Emily’s superpower is simple. She watches a stupid amount of horse races. On the track or on video replays, she spends hours watching and analyzing tape. If there is a horse running in a race somewhere right now, chances are Emily has seen that horse race before. She may have even seen all of its races. And she compiles notes on those races—information that data-driven algorithms don’t have. Information that requires a human eye and a human mind to assess. Information that there is no shortcut to obtain. And information that has given her an almost sixth sense when it comes to analyzing horse races.
Today at Santa Anita, Emily isn’t playing in the $10,000 buy-in Breeders’ Cup Betting Challenge with Garett, so they don’t have to worry about each other. Instead, she’s putting her research and analysis to work to help me and my producers win some grocery money.
There are different types of gamblers. Some gamble for the rush, others for ego, others simply for the money. Gamblers that I relate to most, gamblers like Emily, love to play games. Learning the rules, coming up with a strategy, and putting your ideas to the test. Horse racing presents these types of gamblers with all they could ever wish for. There is a ton of data available to analyze. And because the odds aren’t fixed, but fluctuate based on how everyone bets, when you’re right about something that everyone else is wrong about, you can make a pile of money. Despite what you may think from seeing the stereotypical railbird at the track—the big-mouthed touts, or the high rollers in fancy suits, or the old guys in their polyester shirts and blue blocker shades—those guys are all square. They’re dead money. It’s the true fucking nerds who hoover up all the money in this game. The ones with spreadsheets, and charts, and graphs, and a keen sense of value and opportunity. For all the colorful characters and weekend warriors you meet at the track, it’s the ones in the background, the ones like Emily, who are doing the work to win.
To hear the full Emily Gullikson episode, click here, and be sure to follow on Spotify and check back every Wednesday for new Gamblers episodes. This excerpt has been lightly edited for clarity and length.